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<h1><a href="https://archiveofourown.org/works/29313711">The One With Their First Time</a> by <a class='authorlink' href='https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell'>HolyFuckingHell</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Dean and Cas’s Time [9]</td></tr>

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Sex, Awkward, Awkward First Times, Awkward Sexual Situations, Awkwardness, Blow Jobs, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Cuddling &amp; Snuggling, First Time, Fluff, Fluff and Smut, Hand Jobs, Kissing, M/M, Making Out, Oral Sex, Sex, Smut, Spooning, Top Dean Winchester</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2021-02-09</td></tr>

<tr><td><b>Updated:</b></td><td>2021-02-09</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-13 09:02:28</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>8,510</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/29313711</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean and Cas have been dating for a little bit at this point, but this is the first time they have sex. Actual, real, full-blow sex. Cas tells Dean he's ready which Dean was... Not expecting.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel &amp; Dean Winchester, Castiel/Dean Winchester</td></tr>

<tr><td><b>Series:</b></td><td>Dean and Cas’s Time [9]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/2069001</td></tr>

<tr><td><b>Comments:</b></td><td>16</td></tr>

<tr><td><b>Kudos:</b></td><td>131</td></tr>

</table>

<a name="section0001"><h2>The One With Their First Time</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Y'all, I hate summaries. I'm not good at them, and I hate them so I apologize for how bad they are. Anyway! Thanks for reading! I hope you like this one!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>
  <span>Dean is quite happy to find out that Cas initiates sex just about as much as Dean does. He really didn’t expect that at all, but it’s a nice surprise. It’s become an every night thing for Cas to come to Dean’s room with him, even if it’s just to make out a little before Dean goes to sleep. </span>
</p><p>
  <span>It. Is. Fantastic. They make out randomly throughout the day then at night they make out, of course, that's a longer, more sloppy session, and Dean loves it just as much. And sometimes their sloppy make-out sessions turn into sloppy blowjobs. Sometimes it’s Cas giving the blowjob, sometimes it’s Dean, sometimes it’s both. And Cas has gotten the light-bulb thing under control. The first time after their first time ever (once Dean changed the bulbs,) all the lights did was flicker. Then after that, they did nothing. Cas is truly relieved he got that under control, but Dean thought it was kinda cool. </span>
  <em>
    <span>Destructive,</span>
  </em>
  <span> yes, but still cool.</span>
</p><p>
  <span>The thing though is that Cas never stays the night. He always leaves either right before Dean goes to sleep after they finish making out, or he leaves from the bathroom when they accidentally get too messy during blowjobs. Dean thinks it’s a little weird, but he doesn’t say anything about it. Sure he would like Cas to stay with him so they can… Cuddle or whatever. He gets it, Cas doesn’t sleep, it’s probably boring or something. Dean doesn’t </span>
  <em>
    <span>really</span>
  </em>
  <span> like sleeping alone but he has his whole life so, what’s the rest of it?</span>
</p><p>
  <span>At least he gets to make out with Cas every night. Cas is so fun to make out with and he has gotten really good at it. Sam always gets mad at them and begs them not to ‘be disgusting’ in the public areas of the bunker. They try not to, but sometimes they’ll look at each other throughout the day… And they just can’t help it. </span>
</p><p>
  <span>Today, as a matter of fact, they have been making out much more than normal, all kissing initiated by Cas. Dean doesn’t get it until they are in his room later, making out, of course.</span>
</p><p>
  <span>Cas is laying down with Dean pressed on top of him as they make out. Cas usually prefers to be on top of Dean, but this time it’s okay. Cas reaches his hands around Dean and firmly grabs his ass through his jeans. Cas has never done this before and it makes Dean blush but he doesn’t say anything because he doesn’t want Cas to stop. “Dean, do you ever want to do…” Cas looks nervously away for a second. “Do you ever want to do more?”</span>
</p><p>
  <span>More? Like more blowjobs? Or spend more time making out? Dean would do that. Or maybe Cas wants to spend the whole night with him! That would rock. “What do you mean ‘more?’” Dean asks finally. “Like </span>
  <em>
    <span>make out</span>
  </em>
  <span> more?” Dean licks his lips. </span>
</p><p>
  <span>Cas pauses. “Yes…” Cas sighs, “‘Like make out more,’” He nods.</span>
</p><p>
  <span>“Were you talking about something else?” Dean asks. </span>
</p><p>
  <span>“No,” Cas lies.</span>
</p><p>
  <span>“I feel like maybe you were…” Dean says.</span>
</p><p>
  <span>“No,” Cas shakes his head. </span>
</p><p>
  <span>“Okay…” Dean smiles then moves to Cas’s neck to kiss him there.</span>
</p><p>
  <span>“What is this?” Cas says confused. Dean keeps kissing softly around Cas’s neck. “Oh,” Cas swallows and tilts his head up so Dean has more room. “This feels pleasant,” Cas hums. “Do you enjoy this as well?”</span>
</p><p>
  <span>Dean, again, doesn’t say anything. Cas grumbles then holds tightly to Dean, flipping them both over quite quickly. “Woah,” Dean pants. </span>
</p><p>
  <span>“I asked you a question.”</span>
</p><p>
  <span>“Hm…” Dean squeaks. He’s pretty turned on right now.</span>
</p><p>
  <span>Cas grumbles again then starts kissing Dean’s neck. Dean hums and seems like he is enjoying it so Cas continues. </span>
</p><p>
  <span>“Oh, Cas,” Dean hums slowly. </span>
</p><p>
  <span>Cas eventually pulls away, a bit shocked as he looks down at Dean. “Oh, no…” Cas tilts his head, “You have bruises…”</span>
</p><p>
  <span>“What?” Dean says confused. </span>
</p><p>
  <span>“I think they are my fault because they were not there when I started,” Cas grimaces and reaches for Dean to heal him of them. “I can fix it-”</span>
</p><p>
  <span>Dean grabs Cas’s hand to stop him. “Wait…” Cas pulls his hand back. “Hickies? Did you give me hickies?”</span>
</p><p>
  <span>“Are hickies bruises?” Cas asks. </span>
</p><p>
  <span>“Kinda…” Dean laughs. “Cas… I think you gave me hickies!” </span>
</p><p>
  <span>“I apologize, Dean. I will remove them now-”</span>
</p><p>
  <span>“No, wait!” Dean says again. “Leave them. At least until the end of the night…”</span>
</p><p>
  <span>“Why?” Cas asks. </span>
</p><p>
  <span>“Cas, dude, you marked me…” Dean chuckles. “And it’s kinda fun…”</span>
</p><p>
  <span>“Oh!” Cas smiles and starts kissing there again but only for a moment before he decides to start taking Dean’s pants off. Dean gets excited and shifts how he’s sitting to help Cas get his pants down a bit. Cas sort of smirks when he sees Dean's dick. Dean blushes. Cas does it every time and it makes Dean feel kinda funny about it. He wonders if Cas will ever stop looking at him like that but he will later find out that Cas won’t. Cas will always love the moment Dean gets even just </span>
  <em>
    <span>somewhat</span>
  </em>
  <span> naked. </span>
</p><p>
  <span>Cas holds firmly on Dean’s dick and strokes until he feels it get hard. Dean gazes at him softly, eyes partly closed. “Mm…” Dean hums. </span>
</p><p>
  <span>Cas licks his lips and leans over to suck Dean off. Then when Dean comes, for the first time ever Cas decides he’s going to swallow. And when he does, Dean almost dies. He’s panting and babbling at Cas, Cas just smiles and giggles, crawling up next to him. “Did you enjoy that?” Cas asks. </span>
</p><p>
  <span>“Yeah…” Dean swallows and nods. “Yeah, I- You swallowed it? All of it?”</span>
</p><p>
  <span>“All of your ejaculate? Yes, I did.”</span>
</p><p>
  <span>“Oh my god…” Dean pants as he pulls his underwear back up and decides to pull his pants completely off. </span>
</p><p>
  <span>“Please don’t say that,” Cas cringes. </span>
</p><p>
  <span>“Okay,” Dean nods. “Sorry.”</span>
</p><p>
  <span>“But that felt nice?” Cas lays into Dean. </span>
</p><p>
  <span>“Yeah…” Dean nods. “Do you want-”</span>
</p><p>
  <span>“Dean,” Cas interrupts. “I want more than that.” There Cas goes again with the ‘more’ stuff. Dean doesn’t understand what he means. “So when you are ready…” Cas looks away shyly, “Do not hesitate to tell me.”</span>
</p><p>
  <span>“‘More?’” Dean asks again. </span>
</p><p>
  <span>“I would like to have sex with you. </span>
  <em>
    <span>Full</span>
  </em>
  <span> fornication.” Cas says bluntly. </span>
</p><p>
  <span>So, apparently, when Cas is trying to hint at stuff, </span>
  <em>
    <span>those</span>
  </em>
  <span> are the days that he kisses Dean a whole bunch. Dean is now making that connection. “F-” Dean nods, “‘Full fornication,’ okay…” </span>
</p><p>
  <span>“Not tonight,” Cas snuggles into Dean even more, “It does not have to be tonight. I only wish you will tell me when you would like to try…”</span>
</p><p>
  <span>“Okay,” Dean nods. </span>
</p><p>
  <span>“Alright,” Cas kisses him for a brief moment before he gets up. “I will see you in the morning.”</span>
</p><p>
  <span>So </span>
  <em>
    <span>Dean</span>
  </em>
  <span> has a lot to think about. </span>
  <em>
    <span>Hm!</span>
  </em>
  <span> Cas is ready right now? Cas wants to </span>
  <em>
    <span>do it. </span>
  </em>
  <span>Like, </span>
  <em>
    <span>do it</span>
  </em>
  <span> do it! Cas is ready before Dean! Dean can’t believe this. How is Cas ready before he is? He definitely thought it would be the other way around…</span>
</p><p>
  <span>Dean knows he </span>
  <em>
    <span>wants</span>
  </em>
  <span> to have sex with Cas, like </span>
  <em>
    <span>more</span>
  </em>
  <span> than just third base sex. He does. But wanting it and doing it are different! Sure, Dean thinks about it a lot. Thinks about how that would play out, how it would feel, how… Big Cas’s dick is… That scares him a little bit, but that’s not the part that's holding him back. </span>
</p><p>
  <span>Truth be told, Dean doesn’t know what’s holding him back. Sure, he lacks experience but so does Cas, so… It should be okay! He’s never… </span>
  <em>
    <span>Had</span>
  </em>
  <span> sex with a dude, but he knows… Kind of how it’s supposed to go. Enough to get by at least… Dean has lube in case the moment ever overcame them or in case they maybe wanted it for better handjobs or something. Spit works for handjobs but Dean knows it’s not the same for sex. </span>
</p><p>
  <span>Now that he’s thinking about it though, he and Cas have never given handjobs, they’ve been doing strictly oral. Maybe Dean should give Cas a handjob just to see. </span>
</p><p>
  <span>Point is, Dean wants to buck up and get ready. He </span>
  <em>
    <span>wants</span>
  </em>
  <span> to have sex with Cas. He’s just… Kinda scared. </span>
</p><p>
  <span>The next day happens completely normally. Cas doesn't obsessively kiss him because he’s got nothing to hint at anymore. At least, Dean thinks he doesn’t. Then later that night, Cas doesn’t even bring it up. Dean kinda wants to talk about it, but he doesn’t want to be the one to bring it up, he wants </span>
  <em>
    <span>Cas </span>
  </em>
  <span>to bring it up!</span>
</p><p>
  <span>But he never does. Then the conversation dies down and it seems like Cas is about to leave. </span>
</p><p>
  <span>“Okay-” Cas starts as he moves to get up. </span>
</p><p>
  <span>“No!” Dean says quickly, grabbing Cas’s arm. “Uhm, let me…” Dean starts messing with the buttons of Cas’s pants but is struggling to get them off. </span>
</p><p>
  <span>Cas watches as Dean struggles for a moment, then he unbuttons his own pants and takes them off. Dean rolls his eyes, a bit upset he couldn’t do it on his own, but he lets that go. Dean climbs onto Cas’s lap, straddling his thighs and kissing him again. </span>
</p><p>
  <span>“Wait, </span>
  <em>
    <span>shit,”</span>
  </em>
  <span> Dean rolls his eyes then gets off of Cas. </span>
</p><p>
  <span>“What are you doing?” Cas asks curiously. </span>
</p><p>
  <span>Dean opens the drawer on his nightstand and pulls out the lube, shutting the drawer quickly. “Getting this so I can… Jack you off better…”</span>
</p><p>
  <span>“Lubrication?”</span>
</p><p>
  <span>“Yes,” Dean climbs back over Cas and takes off his shirt.</span>
</p><p>
  <span>“‘Jacking off’ is manual stimulation, correct?” Cas asks. Dean starts working on the buttons of Cas’s shirt but he sucks at that too, so Cas takes over. </span>
</p><p>
  <span>“Yes, handjobs, yeah,” Dean nods. </span>
  <em>
    <span>“Fuck.”</span>
  </em>
  <span> Dean decides to just slide Cas’s tie off instead since he’s obviously bad at undressing him. </span>
</p><p>
  <span>“Okay,” Cas smiles, “We haven't done this before…”</span>
</p><p>
  <span>“Yeah…” Dean smiles, spreading Cas’s shirt, jacket, and coat as wide as he can to expose his chest as much as possible. “Mm…” Dean hums, putting a bit of lube into his palm, “You can use spit for this, but lube feels better, trust me.”</span>
</p><p>
  <span>“I trust you,” Cas smiles and nods. Dean blushes and rolls his eyes. </span>
</p><p>
  <span>“Okay,” Dean bites his lip as he wraps his hand around Cas’s dick and starts stroking. He can feel Cas’s dick harden slowly and to be honest, it's kinda hot… Cas dick just stiffening up in his hand while Dean is sitting on him… He should kiss him. He should kiss him while he jacks him off. “Feel good?” Dean checks. </span>
</p><p>
  <span>“Oh yes,” Cas nods and he closes his eyes. Dean leans forward and presses their lips together in a slow but deep kiss. </span>
</p><p>
  <span>Like Cas always does, he lasts a while. Dean is of course fine with it especially since giving Cas a handjob right now isn’t exactly exhausting. And he likes that he gets to kiss him while he does this. Maybe Dean should give him handjobs every night like standard. Like kissing. Cas really seems to like this. </span>
</p><p>
  <span>Cas has been holding around Dean’s waist and his grip gets tighter when he’s about to come. “Mff,” Cas pulls away from their kiss. “I am about to ejaculate…” </span>
</p><p>
  <span>“Good,” Dean grins as he meets Cas’s lips again. When Cas finally does, it squirts between them, mostly landing on Dean’s stomach. “Nice…” Dean smiles genuinely. </span>
</p><p>
  <span>“You are very good at that,” Cas smiles. </span>
</p><p>
  <span>“Thanks. Years of practice, you know?”</span>
</p><p>
  <span>“How many years? When did you start masturbating?”</span>
</p><p>
  <span>“That’s a weird question, Cas,” Dean chuckles nervously. </span>
</p><p>
  <span>“Sorry, I didn’t mean to make you uncomfortable. I was simply curious.”</span>
</p><p>
  <span>“Uhm,” Dean wiggles nervously. “When I was thirteen I realized it felt </span>
  <em>
    <span>really</span>
  </em>
  <span> good when I um…” Dean rolls his eyes, “But I didn’t really start… You know… Until I was like fifteen…”</span>
</p><p>
  <span>“That seems like a large gap.”</span>
</p><p>
  <span>“Yeah well, we were always busy so I never </span>
  <em>
    <span>made </span>
  </em>
  <span>time until I </span>
  <em>
    <span>had</span>
  </em>
  <span> to.”</span>
</p><p>
  <span>“‘Had to?’ It sounds like something overcame you.”</span>
</p><p>
  <span>“Yeah,” Dean chuckles. “I was a teenager. I was horny all the time!”</span>
</p><p>
  <span>“You make it sound like that went away when in reality you are still very horny…” They both chuckle. “Right, Dean?” Cas reaches for Dean’s pants to take them off but Dean stops him. </span>
</p><p>
  <span>“No, wait…” Dean swallows. “I think we should talk…” He looks down and away.</span>
</p><p>
  <span>“You want to talk? About what?”</span>
</p><p>
  <span>“No,” Dean chuckles. “I don’t </span>
  <em>
    <span>want</span>
  </em>
  <span> to talk… I just think we should.”</span>
</p><p>
  <span>“Alright,” Cas nods, feeling up Dean’s sides where his hands still are. He likes to touch Dean but Dean finds it actually kind of comforting. </span>
</p><p>
  <span>“I know you want to… Like…” Dean swallows. </span>
  <em>
    <span>“Fuck.</span>
  </em>
  <span> And </span>
  <em>
    <span>I</span>
  </em>
  <span> want to… Too. But right now I just… Kinda…”</span>
</p><p>
  <span>“It’s okay if you are not ready, Dean,” Cas smiles. </span>
</p><p>
  <span>“It is?”</span>
</p><p>
  <span>“Absolutely,” Cas nods sternly.</span>
</p><p>
  <span>“Okay well… I don’t want you to think that like… I don’t like you or something…”</span>
</p><p>
  <span>“I would not have thought that,” Cas pokes a finger into the come that's dripping down Dean’s stomach. </span>
</p><p>
  <span>“Okay…” Dean leans into Cas pressing their chests together like a lazy hug. Cas wraps his arms around Dean. “I’m sorry…”</span>
</p><p>
  <span>“There is no reason to be sorry,” Cas says, lifting Dean up as he stands up. </span>
</p><p>
  <span>“Holy fuck, you’re strong…” Dean admires. “What are you doing?” Dean wraps his legs around Cas. </span>
</p><p>
  <span>Cas uses one hand to awkwardly pull his pants up. “Taking you to the bathroom…”</span>
</p><p>
  <span>“Well you ain’t gotta carry me there… I can walk…” Dean says but Cas’s arms are </span>
  <em>
    <span>already</span>
  </em>
  <span> around him and he is </span>
  <em>
    <span>already</span>
  </em>
  <span> walking to the door. </span>
</p><p>
  <span>“Yes, you </span>
  <em>
    <span>can</span>
  </em>
  <span> walk, but I </span>
  <em>
    <span>can</span>
  </em>
  <span> carry you…” Cas says. Dean sighs happily, wrapping his arms over Cas’s shoulders and settling his head in his arm. Dean just hopes Sam and Jack are both actually in bed and aren’t out there to potentially witness this. Luckily, they aren’t. </span>
</p><p>
  <span>The nights that follow are still very fun. Them just making out… Being close… Dean giving Cas handjobs and blowjobs like his life depends on it. Cas loves how much attention Dean gives to these sorts of things. One night, Dean makes Cas come earlier in the night but they wound up talking for a while after so Cas didn’t leave right away. Then like, fifteen minutes later Dean gives him a blowjob and he comes </span>
  <em>
    <span>again. </span>
  </em>
  <span>That's the night Dean finds out Cas recovers so effing quickly. Dean couldn’t even </span>
  <em>
    <span>dream</span>
  </em>
  <span> of being able to get it up fifteen minutes after. Maybe when he was younger but definitely not now.</span>
</p><p>
  <span>Cas on the other hand is slightly confused because Dean won’t let Cas do anything to him. Every time he tries, Dean stops him and says that he is ‘okay.’ But Cas doesn’t bring it up.</span>
</p><p>
  <span>Well, he doesn’t bring it up to </span>
  <em>
    <span>Dean. Sam</span>
  </em>
  <span> on the other hand gets an earful. </span>
</p><p>
  <span>“Sam, I would like to talk again…” Cas sits down across from Sam. </span>
</p><p>
  <span>Sam knows what he means. They actually talk all the time, it’s just that when Cas wants to talk about his relationship-y stuff, that’s what he says. Sam finds it funny because Dean does </span>
  <em>
    <span>the same thing</span>
  </em>
  <span> when he wants to, too. Dean does it </span>
  <em>
    <span>way less</span>
  </em>
  <span> than Cas. Cas will just talk about what happens because they are friends and he thinks that’s what friends do. And he’s right… To an extent. Dean though, Dean only comes to Sam when he’s desperate or needs advice of some kind. </span>
</p><p>
  <span>“No, Cas,” Sam shakes his head, “Talking is reserved for people who </span>
  <em>
    <span>do not</span>
  </em>
  <span> make out grossly in our motel rooms just because you thought Jack and I were </span>
  <em>
    <span>‘sleeping.’”</span>
  </em>
  <span> Sam uses finger quotes. </span>
</p><p>
  <span>“We apologized!” Cas chuckles. “It won’t happen again…”</span>
</p><p>
  <span>“It better not,” Sam rolls his eyes. “Fine, what’s up?” </span>
</p><p>
  <span>“Well, Dean started giving me handjobs recently and-”</span>
</p><p>
  <span>“Already too much detail,” Sam interrupts. </span>
</p><p>
  <span>“I don’t understand what you find appropriate and what you do not find appropriate.”</span>
</p><p>
  <span>“Specifics. Try </span>
  <em>
    <span>not </span>
  </em>
  <span>to paint a picture. I don’t want to be able to see it clearly in my head.”</span>
</p><p>
  <span>“Okay…” Cas nods, “But I feel as though that detail is important.”</span>
</p><p>
  <span>“Oh god,” Sam rolls his eyes, “This is gonna be a messed up conversation, I already know.”</span>
</p><p>
  <span>“Okay, I’ll only tell you the </span>
  <em>
    <span>most</span>
  </em>
  <span> important details.”</span>
</p><p>
  <span>“Thank you.”</span>
</p><p>
  <span>“Almost a week ago I told Dean that I would like to start having sex. Of course, only if he is ready, which he informed me that he is not. And since then, Dean has not let me pleasure him in any way.”</span>
</p><p>
  <span>“I have so many questions but I am afraid of all of them,” Sam looks around then leans in towards Cas to whisper. “I thought you guys were already having sex… What have you guys been doing?”</span>
</p><p>
  <span>Cas tilts his head. “I talked to you about this one day after it happened…” Cas makes a face. “Do you not remember?”</span>
</p><p>
  <span>“Oh!” Sam recalls. That weird conversation they had is all starting to make sense. It’s just that </span>
  <em>
    <span>before,</span>
  </em>
  <span> he had talked to Dean. Dean didn’t really confirm or deny anything so Sam just assumed they had had sex. He didn’t think any more of it because he didn’t want to because that’s gross. Then the next day Cas told Sam that his idea of getting naked worked! And some other stuff. “That’s right…” Sam nods, “You guys have just been doing like… Oral…” Sam is horrified. He knows too much about their relationship, bleh!</span>
</p><p>
  <span>“Yes…” Cas nods. </span>
</p><p>
  <span>“Okay, well…” Sam constructs his next question slowly. “So… </span>
  <em>
    <span>You</span>
  </em>
  <span> are ready to… You know… But he’s not?”</span>
</p><p>
  <span>“He is not.”</span>
</p><p>
  <span>“He said that?”</span>
</p><p>
  <span>“Yes.”</span>
</p><p>
  <span>“Ohh…” Sam shrugs. He never would have thought that’d be the case. Not that he tries to think about the case because again, bleh. “And he doesn’t want you… Doing anything to him?”</span>
</p><p>
  <span>“Correct.”</span>
</p><p>
  <span>“Does he do stuff to you, still?”</span>
</p><p>
  <span>“Every night.”</span>
</p><p>
  <span>“Agh,” Sam groans and shakes his head, “See, that’s… Again, that’s too much detail, Cas. A ‘yes’ would have been fine!”</span>
</p><p>
  <span>“My apologies.”</span>
</p><p>
  <span>“So have you asked him why he won’t let you… Do stuff… Anymore?”</span>
</p><p>
  <span>“No, I haven’t,” Cas shakes his head. </span>
</p><p>
  <span>“Well, then ask him.”</span>
</p><p>
  <span>“No,” Cas shakes his head, “Because he doesn’t like talking about this kind of stuff!”</span>
</p><p>
  <span>“Uh, newsflash, Giacomo! I don’t like talking about this stuff either!” Sam rolls his eyes. </span>
</p><p>
  <span>“Oh, Right…” Cas says sadly. </span>
</p><p>
  <span>“But!” Sam huffs, “I do it anyway… Because I am your friend.”</span>
</p><p>
  <span>“Thank you, Sam.” Cas half-smiles at him. </span>
</p><p>
  <span>“Yeah,” Sam rolls his eyes. “But, Dean… Dean will </span>
  <em>
    <span>also</span>
  </em>
  <span> talk to you about it because he and you are together.”</span>
</p><p>
  <span>“So I should just ask him why he will not let me pleasure him?”</span>
</p><p>
  <span>Sam grumbles. “Yes.”</span>
</p><p>
  <span>“Okay,” Cas nods, “Thank you…” </span>
</p><p>
  <span>The conversation seems to be over or at least… Over-ish. “Good luck with the whole… Sex thing though…” Sam shakes his head. This is the weirdest possible conversation. </span>
</p><p>
  <span>“Thank you, Sam!” Cas smiles. </span>
</p><p>
  <span>So then later when they are in Dean’s room, they’re making out and Dean is on Cas’s lap with his hand down Cas’s open pants. </span>
</p><p>
  <span>“Wait,” Cas pulls away, “Let me…” Cas starts opening Dean’s pants but Dean grabs his wrists to stop him. </span>
</p><p>
  <span>“No, Cas…” Dean says softly, getting his lips closer to Cas’s, “I’m okay, babe, just you right now…” Dean kisses him and starts to get his hand back into Cas's pants and Cas lets him because he is distracted by the whole ‘babe’ thing. </span>
</p><p>
  <span>“Dean,” Cas pulls away. “Why have you stopped me from performing fellatio for the past week? You have stopped me from pleasuring you at all!”</span>
</p><p>
  <span>“I…” Dean makes a face and shakes his head, “I don’t know what you’re talking about…” </span>
</p><p>
  <span>“Is this because you do not enjoy it?” Cas tilts his head. </span>
</p><p>
  <span>“What?” Dean says quickly, “No! I love it!”</span>
</p><p>
  <span>“Oh,” Cas nods moving for Dean’s pants again, “So then you will enjoy if I-”</span>
</p><p>
  <span>“But!” Dean says quickly, stopping Cas again. “We’re doing </span>
  <em>
    <span>you</span>
  </em>
  <span> tonight…” Dean starts crawling down to give Cas a blowjob. </span>
</p><p>
  <span>“Dean,” Cas sighs, “Please talk to me. I don’t like this…”</span>
</p><p>
  <span>“Don’t like what?” Dean panics. He doesn’t like the blowjobs! Or the handjobs! He thinks Dean is bad at it! Or he doesn’t like the kissing! Oh no! </span>
</p><p>
  <span>“I don’t like the subtlety. Or whatever else this is. From here on, can you and I be forward with each other?” Cas swallows. “I want to know what you want and how you feel because I am not sure I can figure it out on my own. For example, if you want fellatio, expressly ask. Or if you would like to be held,” Dean blushes, “Say so.”</span>
</p><p>
  <span>“Okay,” Dean nods. That makes a lot of sense, how can he say no?</span>
</p><p>
  <span>“And I will do the same. Now, please,” Cas looks into Dean’s eyes. “Why won’t you let me pleasure you?” </span>
</p><p>
  <span>Dean looks away… “‘Cause… Because…” Dean groans, this is harder to admit than he thought. “Because you are ready to have sex- </span>
  <em>
    <span>Which is great!”</span>
  </em>
  <span> Dean says quickly. “But I’m… Not. And I want to give you what you want but I can’t yet…” Dean looks back at Cas. “So I feel bad.”</span>
</p><p>
  <span>“Oh,” Cas nods. “But, Dean,” Cas tilts his head, “That doesn’t make any sense. </span>
  <em>
    <span>You</span>
  </em>
  <span> are what I want so by stopping me-”</span>
</p><p>
  <span>“Oh,” Dean interrupts, “I see now… Okay.”</span>
</p><p>
  <span>“Also,” Cas smiles and gets closer to Dean, “It’s alright if you are not ready… I was simply trying to tell you that </span>
  <em>
    <span>I</span>
  </em>
  <span> would like to so if you are ready, we can do it. I wasn’t trying to make you feel uncomfortable…”</span>
</p><p>
  <span>“It’s just,” Dean swallows, “You’re not nervous about this at all and </span>
  <em>
    <span>I</span>
  </em>
  <span> am!”</span>
</p><p>
  <span>“What?” Cas asks. “I </span>
  <em>
    <span>am</span>
  </em>
  <span> nervous! I’m terrified!”</span>
</p><p>
  <span>“You are?!” Cas nods. “Well you don’t </span>
  <em>
    <span>seem</span>
  </em>
  <span> nervous!” Dean exasperates. “You act like boning is just </span>
  <em>
    <span>something</span>
  </em>
  <span> to do!”</span>
</p><p>
  <span>Cas doesn’t know what that means but he uses context clues, “Well, isn’t it?” In its most literal sense, yes. </span>
</p><p>
  <span>“No!” Dean shouts, “It’s a big deal!” </span>
</p><p>
  <span>“Yes, I agree!” Cas smiles, “But at the end of it all, it’s just pleasure… And we are already doing that…”</span>
</p><p>
  <span>“You-” Dean pauses, calming down and mumbling softly, “You’re right…” </span>
</p><p>
  <span>“It’s a </span>
  <em>
    <span>new</span>
  </em>
  <span> kind of pleasure which stems nerves, but it’s all the same…”</span>
</p><p>
  <span>“But like… </span>
  <em>
    <span>Butt stuff?</span>
  </em>
  <span> That doesn’t freak you out?”</span>
</p><p>
  <span>“Not necessarily.”</span>
</p><p>
  <span>“So you’re… You’re cool with it?” Dean asks. Cas nods sternly. “So,” Dean looks away. He’s actually been </span>
  <em>
    <span>super</span>
  </em>
  <span> curious about this… “Maybe we should…” Dean gulps, “Maybe we should try it…”</span>
</p><p>
  <span>“Right now?” Cas asks. </span>
</p><p>
  <span>“If you want…” Dean says nervously. </span>
</p><p>
  <span>“Yes!” Cas agrees excitedly, “If you are comfortable with that, then yes!”</span>
</p><p>
  <span>“Okay,” Dean nods. “Uhm…” Dean gulps, “You get naked first, then I’ll… do it.”</span>
</p><p>
  <span>“Okay…” Cas agrees then starts taking off all his clothes. Cas is almost naked when Dean finally starts taking his pants off. “How would you like this to be done?” Cas asks Dean. </span>
</p><p>
  <span>“Hm?” Dean is confused for a second. </span>
</p><p>
  <span>“Would you like me to enter you, or would you like to enter me?” Cas asks, really taking the forwardness to heart. This is just Cas’s weird way of asking ‘top or bottom,’ except </span>
  <em>
    <span>really uncomfortable!</span>
  </em>
</p><p>
  <span>“Oh…” Dean blushes very hard again. He feels a little awkward now, thanks Cas. “How d- H- How do you wanna… Do it?” Dean asks. </span>
</p><p>
  <span>“However you would like to!” Cas is finally naked and looks back up at Dean. Dean has stopped undressing and is now in only his underwear and socks. </span>
</p><p>
  <span>“I wanna… Fuck </span>
  <em>
    <span>you…</span>
  </em>
  <span> Is that okay?”</span>
</p><p>
  <span>“It’s perfect!” Cas cheers, walking over to Dean. </span>
</p><p>
  <span>“Unless you want…” Dean swallows. “Unless you wanna like… Do it. I guess.”</span>
</p><p>
  <span>“I would like to do it either way!” Cas holds Dean’s underwear and starts pulling them slowly down.</span>
</p><p>
  <span>“O- Okay,” Dean nods shyly. “Are you sure?” Dean asks. </span>
</p><p>
  <span>“Absolutely, yes!” Cas kisses him and drags him down with him on the bed. </span>
</p><p>
  <span>The kissing helps with Dean’s nerves a little bit but he’s still freaking out about this. He’s about to have sex with a guy. Like </span>
  <em>
    <span>real</span>
  </em>
  <span> sex. </span>
  <em>
    <span>Real</span>
  </em>
  <span> sex with a </span>
  <em>
    <span>guy. </span>
  </em>
</p><p>
  <span>After a few minutes of making out Dean is starting to realize he is </span>
  <em>
    <span>wildly </span>
  </em>
  <span>unprepared. He doesn’t know what he’s </span>
  <em>
    <span>doing!! </span>
  </em>
  <span>What the hell? </span>
</p><p>
  <span>“Um,” Cas sits up. “Where do you keep your lubricant? In this drawer?” </span>
</p><p>
  <span>“No!” Dean says quickly so Cas pulls his hand back. “I’ll- I’ll get it!” Well, that’s not suspicious at all. Dean wiggles out from under Cas. “Just like… Lay down and I’ll get it…” Dean stands up. </span>
</p><p>
  <span>“Okay…” Cas smiles, laying down on the bed, nervously excited. </span>
</p><p>
  <span>“Okay,” Dean mumbles to himself as he pulls the drawer open. Maybe he would have let Cas get it but not too long ago, actually like, the day before Cas said he was ready, Dean purchased a dildo from a store online. It just came in pretty recently. Dean freaked out when he saw it. He hasn’t taken it out of the box and he </span>
  <em>
    <span>definitely</span>
  </em>
  <span> hasn’t used it. It’s currently just sitting in his drawer. </span>
</p><p>
  <span>What can he say, he got curious? He knew at some point they would… You know… So he was thinking about it… He doesn't really know why he bought it. </span>
</p><p>
  <span>Point is, Cas can’t know. So, </span>
  <em>
    <span>Dean</span>
  </em>
  <span> will be getting the lube. </span>
</p><p>
  <span>Dean pulls out his lube and a condom and crawls back over to Cas. “Okay, so like…” Dean blushes and he’s shaking a little bit. “I think I gotta… You know… Like… Get you… Ready…”</span>
</p><p>
  <span>“Okay,” Cas nods and spreads his legs. “Is this position alright?” Cas asks. </span>
</p><p>
  <span>“I don’t know…” Dean glances away, “Do you wanna be on your hands and knees?”</span>
</p><p>
  <span>“Would that be better?” Cas asks. </span>
</p><p>
  <span>“It might be, like… Easier…” Dean doesn’t know. </span>
</p><p>
  <span>“Okay,” Cas nods and turns over, getting into the position Dean suggested. “We can’t face each other this way, but that’s okay…” </span>
</p><p>
  <span>“Have you…” Dean cringes. “Have you ever done like, </span>
  <em>
    <span>anything</span>
  </em>
  <span> in the way of… Your ass?”</span>
</p><p>
  <span>“No,” Cas shakes his head. “Have you?”</span>
</p><p>
  <span>“No,” Dean pauses. He takes a deep breath and gets some lube out and onto his fingertips. “Ready?” He asks. </span>
</p><p>
  <span>“Yes.”</span>
</p><p>
  <span>“Okay,” Dean finally looks at Cas’s ass. And holy fuck. He’s not grossed out or anything, he’s actually kinda turned on. Cas has a </span>
  <em>
    <span>really</span>
  </em>
  <span> nice ass. Dean gets distracted from his nervousness as he reaches out with his clean hand to touch him. He glides his hand firmly over one of Cas’s cheeks and feels somewhat mesmerized by it. “Mm,” Dean hums. Cas smiles to himself. Dean likes his ass, that’s nice. </span>
</p><p>
  <span>Then Dean refocuses. He doesn’t quite know what to do and he’s feeling like a gist isn’t even enough anymore. He smears the lube over Cas’s hole. </span>
</p><p>
  <span>Okay, he did that. He touched a dude’s asshole. Now he’s just gotta… Um… Finger him open or something. </span>
</p><p>
  <span>Hopefully it’s like fingering a girl. He’s fingered chicks before so if it’s anything close to the same thing, he can totally do this. Usually he would start with two fingers but… He looks at Cas’s hole again and quickly decides he should just start with one. He looks really tight. </span>
</p><p>
  <span>“Are you alright, Dean?”</span>
</p><p>
  <span>“What- Yeah,” Dean swallows, “Yeah, sorry.”</span>
</p><p>
  <span>“That’s alright, take all the time you need.” Well, Dean doesn’t just want to awkwardly stare at a guy's asshole forever so he should probably do something. He just needs to… Do it. </span>
</p><p>
  <span>The lube is sliding down slowly in all the time Dean is just wasting. “Okay,” Dean gulps. He can do this. It’s just like fingering a girl. It’s just like fingering a girl. It’s just like fingering a girl. </span>
</p><p>
  <span>Dean holds onto Cas’s waist and after a moment of courage, Dean pushes a finger into Cas. Then slowly pulls it completely out. “Cas,” Dean tries not to chuckle. “I think you gotta relax a little bit.”</span>
</p><p>
  <span>“Sorry,” Cas apologizes. </span>
</p><p>
  <span>“It’s fine, you’re just… I can’t really finger you,” Dean exhales like a laugh but stops quickly. “If you’re like… Tense.”</span>
</p><p>
  <span>“Okay,” Cas agrees. </span>
</p><p>
  <span>“Wait are you…” Dean bites his lip. “Uhm, like nervous too?”</span>
</p><p>
  <span>“I said that I was earlier, do you not remember?”</span>
</p><p>
  <span>“Oh fuck, I’m sorry,” Dean worries, “I was freaking so much I didn’t… Of course you’d be nervous too. And you definitely </span>
  <em>
    <span>did</span>
  </em>
  <span> tell me that, I’m so sorry.”</span>
</p><p>
  <span>“It’s okay…” Cas smiles but Dean can’t see it. “It’s just my first time and uh, I’m trying to relax. Start again… I will relax.”</span>
</p><p>
  <span>“Okay…” Dean gulps and slides his finger slowly back into Cas. “Yeah, that’s better…” Dean commends. </span>
</p><p>
  <span>Okay, Dean knows that when it comes to fingers, most the chicks he’s been with like pressure better than an in-and-out motion, so he’s just gonna do like… Pressure. Easy enough. Except Dean hasn’t ever fingered a person from this angle before but he starts. It’s a little different than fingering a chick, he decides. The hole is small and tight and also, it’s a dude's ass and Dean is still trying to get over that. </span>
</p><p>
  <span>“I think it would be alright if you added a second finger now,” Cas says. </span>
</p><p>
  <span>Dean is still a little nervous, “Are- Are you sure?” Dean gulps. </span>
</p><p>
  <span>“Yes,” Cas replies.</span>
</p><p>
  <span>“Okay,” Dean holds his breath for a reason he doesn’t know and slides in a second finger. It’s actually really easy and his finger slides in very smoothly. “That okay?” Dean checks. </span>
</p><p>
  <span>“Yes,” Cas hums. </span>
</p><p>
  <span>Good, it feels good. Okay. There’s a lot more Dean can do with two fingers rather than one. He starts working Cas open the best he knows how. He has no idea how this feels because he’s never done anything close to it so he’s just guessing. He’s just… Guessing. </span>
</p><p>
  <span>Cas’s ass. His fingers are in </span>
  <em>
    <span>Cas’s ass</span>
  </em>
  <span> right now. And his heart is beating really fast. And he’s been doing this for a minute or two and has gotten no feedback from Cas. He pulls his fingers out, “Cas, I don’t know how to do this!” Dean panics. </span>
</p><p>
  <span>Cas turns over and sits down to face Dean. “It feels like you do,” Cas tilts his head.</span>
</p><p>
  <span>“It does?”</span>
</p><p>
  <span>“Yes,” Cas nods. “It doesn’t feel bad… It actually feels sort of nice. I would like a tiny bit more at this point if you are still willing.”</span>
</p><p>
  <span>“It really feels nice?” Dean asks. Cas nods. “More?”</span>
</p><p>
  <span>Dean looks really worried right now and Cas doesn’t like that. “We can try a different time if you would like. I don’t mean to rush you.”</span>
</p><p>
  <span>“I want-” Dean sighs and covers his face with his hand. “I want… To </span>
  <em>
    <span>fuck</span>
  </em>
  <span> you. I just… Don’t know how…” </span>
</p><p>
  <span>“What do you mean you ‘don’t know how?’” Cas tilts his head, pulling Dean’s wrist to uncover his face. </span>
</p><p>
  <span>“I mean </span>
  <em>
    <span>I don’t know!</span>
  </em>
  <span> I’ve never </span>
  <em>
    <span>done</span>
  </em>
  <span> this before! I don’t know how to have sex with a </span>
  <em>
    <span>dude!”</span>
  </em>
  
</p><p>
  <span>“Dean,” Cas smiles. “I do believe you are overthinking this…” </span>
</p><p>
  <span>“What?”</span>
</p><p>
  <span>“You know what to do. I’m sure you have some sort of feeling telling you what feels right and what does not…” Cas explains softly. “And if nothing feels right at the moment,” Cas rubs his hand up and down Dean’s thigh comfortingly. “We can try again another time, alright?”</span>
</p><p>
  <span>He’s staring into Dean’s eyes. “Okay,” Dean nods slowly. “You’re right…”</span>
</p><p>
  <span>“Of course I’m right,” Cas crawls up closer to Dean to kiss him again. </span>
</p><p>
  <span>“Wait, Cas,” Dean stops him. “I mean you’re right, I’m overthinking it… Lay back down.”</span>
</p><p>
  <span>Cas smiles, “Okay,” He lays down again, on his back this time, and spreads his legs apart. </span>
</p><p>
  <span>“I can do this, I know how to finger people…” Dean says out loud but mostly to himself. </span>
</p><p>
  <span>“Yes,” Cas nods, “I’m sure you do.” </span>
</p><p>
  <span>“Yeah,” Dean nods, sliding two fingers back into Cas, this time more confidently. </span>
</p><p>
  <span>“This already feels better,” Cas smiles and closes his eyes. </span>
</p><p>
  <span>“It does?” Dean asks excitedly. Cas just hums for confirmation. Dean gazes at Cas. He likes him so much. It’s actually crazy how much. And crazy he never knew. All those years and he never really knew. “Cas,” Dean hums. Then he leans down to kiss Cas. It’s an odd angle to try and finger someone from, but he manages. Cas likes it. He holds onto Dean’s head to pull him close for the kiss -- if that's even possible. He can even feel Cas’s dick harden against him. Dean has been hard for a while, he doesn’t quite know when it happened. </span>
</p><p>
  <span>But eventually, Dean pulls away, sitting back up. He thinks Cas might almost be ready but he just wants to make sure. Dean works his fingers apart inside of Cas and it seems to work fine. “I think you’re ready…” Dean smiles. </span>
</p><p>
  <span>“Good,” Cas nods with a smile in return.</span>
</p><p>
  <span>Dean slides his fingers out and starts getting the condom on. Cas watches him, partly confused, but says nothing. “I’m nervous about this,” Dean swallows but says honestly. </span>
</p><p>
  <span>“Me too,” Cas nods. </span>
</p><p>
  <span>“But I’m also excited,” Dean gets back to Cas, lube in hand. </span>
</p><p>
  <span>“Me too!” Cas agrees. </span>
</p><p>
  <span>“Okay,” Dean’s heart is beating really fast, “I’m gonna add… More lube…” Dean squeezes some out and tosses the bottle to the side.</span>
</p><p>
  <span>Cas twitches at Dean’s sudden touch again as he adds lube. “I’m very ready for this, Dean,” Cas can hardly contain his excitement. Dean smiles because it’s actually really cute when Cas gets like this. </span>
</p><p>
  <span>“Okay,” Dean swallows, lining up with Cas’s hole. “Here we go…” Dean holds onto Cas’s hips.</span>
</p><p>
  <span>“‘Here we go,’” Cas mimics softly. Then Dean slowly pushes into him. Dean groans, Cas hums. Dean pulls out almost completely then pushes back in, this time all the way. “Mm!” Cas groans, “This feels fantastic! Continue!” Cas encourages. </span>
</p><p>
  <span>Dean smiles, he didn’t want to stop and was not planning on it anyway. He starts a steady pace that is pretty slow. </span>
</p><p>
  <span>Cas is so tight around him and it feels insanely good. So tight and warm and good. </span>
  <em>
    <span>“Fuck,”</span>
  </em>
  <span> Dean groans. </span>
</p><p>
  <span>Cas has his legs wrapped around Dean’s sides, pulling him closer almost. “Was that a good ‘fuck’ or a bad ‘fuck?’”</span>
</p><p>
  <span>“Good fuck,” Dean pants. </span>
</p><p>
  <span>“Good,” Cas swallows. Dean feels actually very good inside him, sliding smoothly in and out of him, it feels </span>
  <em>
    <span>really</span>
  </em>
  <span> good. “This is good,” Cas swallows. “This is really good…”</span>
</p><p>
  <span>Dean smiles. “I’m going to speed up a bit, that okay?” </span>
</p><p>
  <span>“Yes,” Cas nods, “Please do.”</span>
</p><p>
  <span>Dean speeds up with a bit shorter thrusts. It feels really, surprisingly good. He didn’t think it was going to feel this good. It feels </span>
  <em>
    <span>so </span>
  </em>
  <span>good. “Mmm… Cas,” Dean grunts. “So good…”</span>
</p><p>
  <span>“Hah,” Cas pants, grabbing onto Dean’s wrists just because he feels like he needs something to hold. “That was something!”</span>
</p><p>
  <span>“What?” Dean asks. </span>
</p><p>
  <span>“Nothing,” Cas shakes his head, “I’ll tell you after… Hah,” Cas swallows. “Do that again.”</span>
</p><p>
  <span>Dean would love to do that again. Whatever he’s doing that Cas likes so much. But he… Doesn’t know what he did. Dean thinks for a second and tries to repeat whatever it was he did. He’s been doing the same thing this whole time, what is there to do again? </span>
</p><p>
  <span>Cas sighs after a second of waiting. “Nevermind, it’s alright…” </span>
</p><p>
  <span>First of all, ouch. He really wanted to do whatever it was that got Cas going. Second, how is Cas talking through sex right now? Oh fuck, Cas has that weird, crazy stamina thing. Dean starts panicking just a little bit. He’s </span>
  <em>
    <span>not</span>
  </em>
  <span> going to last longer than Cas is. He knows he’s not. Dean is always quicker to come than Cas is. So that means, Dean has to do something else to Cas to help him along. </span>
</p><p>
  <span>“Sorry,” Dean pants. </span>
</p><p>
  <span>“No, no!” Cas shakes his head. “This is good, this is wonderful! Don’t apologize.” </span>
</p><p>
  <span>“Hm,” Dean groans. This feels so unbelievably good. Who knew this would be so amazing? What the fucking hell took him so damn long? “Cas,” Dean groans again. Fuck, this is gonna be so embarrassing if he comes this quickly. He should be able to last longer than this, why does he feel so damn close right now? He needs a second to calm down, but </span>
  <em>
    <span>fuck,</span>
  </em>
  <span> he can’t just stop! Dean gazes at Cas for a moment, watching him, eyes closed, his hands still around Dean’s wrists pretty tight. He’s so hot. “Okay,” Dean swallows. He takes his hands off of Cas’s waist which makes Cas let go if his wrists. “Wait, Cas,” Dean grabs Cas’s hands and pins them against the bed above his shoulders. Then Dean leans in and starts kissing Cas. It’s great. It's fun, they both like it, and it gives Dean a reason to break for a second. He’s still </span>
  <em>
    <span>in</span>
  </em>
  <span> Cas, he’s just not moving. They both like the pressure they feel but neither tells the other. </span>
</p><p>
  <span>“Dean,” Cas pants between kisses. “You’re amazing.”</span>
</p><p>
  <span>“No, you are,” Dean breathes, sitting back up. He starts grinding back into Cas again at about the same speed. It’s still pretty slow but it has picked up. They can both feel it just </span>
  <em>
    <span>really</span>
  </em>
  <span> well. Dean wants Cas to come too and he thinks his solution is to just jack Cas off at the same time. </span>
</p><p>
  <span>Cas </span>
  <em>
    <span>loves</span>
  </em>
  <span> his handjobs, this will work great. He thinks this will work </span>
  <em>
    <span>great.</span>
  </em>
  <span> He holds one hand flat at the base of Cas’s dick and starts jacking him off with the other hand, firmly gripped around him. </span>
</p><p>
  <span>“Oh,” Cas’s back arches off the bed, “Dean, hmm…” Cas hums. </span>
</p><p>
  <span>Dean is panting a lot and it’s actually </span>
  <em>
    <span>pretty</span>
  </em>
  <span> embarrassing. </span>
  <em>
    <span>But</span>
  </em>
  <span> Cas seems not to care, so he tries not to be so worried about it. </span>
</p><p>
  <span>Eventually, Dean feels pretty close again and figures it’s probably time this time. “Cas,” Dean swallows.</span>
</p><p>
  <span>Dean doesn’t say anything else after that but Cas has seen him come a couple dozen times so he kind of gets it. “Are you going to come, Dean?” Cas asks. </span>
</p><p>
  <span>Dean is pretty sure Cas doesn’t know how hot that just sounded. “Mhmm,” Dean nods. And a few seconds later he does with a groan. After he calms down a bit from his orgasm he can focus a little more on just Cas. Dean never really stopped jacking him off, but he did get off track and lose rhythm for a few moments. He starts back up again and Cas hums in delight. “Oh, Cas,” Dean admires, looking at him, watching him slowly, </span>
  <em>
    <span>slowly</span>
  </em>
  <span> fall apart on the bed. </span>
</p><p>
  <span>“Dean,” Cas bites his lip. “Can you put your fingers into me again?” Dean smiles, he should have thought of that. It’s nice Cas is asking for it because that has to mean Cas liked it to </span>
  <em>
    <span>some</span>
  </em>
  <span> extent. Dean pushes two fingers back into Cas’s hole making him hum. “Can you… Add a third?” Cas asks politely. </span>
</p><p>
  <span>“Yes,” Dean nods and pushes in a third finger. Cas’s back arches again. Dean is pretty amazed, he always thought three fingers was kinda a lot and the fact Cas can fit that into his </span>
  <em>
    <span>ass</span>
  </em>
  <span> amazes him because his hole was so small and tight before. </span>
</p><p>
  <span>“Okay,” Cas says, his voice deeper and rougher than normal, it kind of turns Dean on, (Or keeps him on.) “I’m going to come.” Dean keeps pumping and a few seconds later, Cas does. And pretty much all of his come lands on his chest. But Dean isn’t seeing that because he’s focused on his lamps again. All of them dimmed for a slow second until they looked pretty much off, then brightened back up </span>
  <em>
    <span>way</span>
  </em>
  <span> brighter than they should, then they went back to their normal brightness. Nothing exploded but Dean still thinks it’s cool. He knows that Cas will be able to get that under control as well just like he did before. Dean takes his fingers out and lets go of him. “Wow,” Cas swallows. </span>
</p><p>
  <span>Dean starts cleaning up, finally taking the condom off as he didn’t have time to do that before. “So…” Dean chuckles, </span>
  <em>
    <span>“That’s</span>
  </em>
  <span> sex…” He kinda wishes he hadn’t said that because it’s goofy and awkward. Luckily, Cas doesn’t seem to mind. </span>
</p><p>
  <span>“Yes,” Cas nods. “It was incredible. It felt so amazing.”</span>
</p><p>
  <span>“Good,” Dean nods, putting the lube back up and pulling on boxers.</span>
</p><p>
  <span>“Where are you going?” Cas asks, still laying still on Dean’s bed. </span>
</p><p>
  <span>“I’m gonna go get you a rag to get you all cleaned up…” Dean half-smiles. </span>
</p><p>
  <span>“Oh, Dean, that’s not necessary, I can just-”</span>
</p><p>
  <span>“No,” Dean interrupts. “I can take care of you- Of it! I can take care of it </span>
  <em>
    <span>for you,”</span>
  </em>
  <span> Dean clears his throat. “I don’t mind.”</span>
</p><p>
  <span>“Yes, but I can-”</span>
</p><p>
  <span>“Cas,” Dean interrupts again, “It’s okay, I </span>
  <em>
    <span>want</span>
  </em>
  <span> to. Just lay right here,” Dean looks out the door, “I’ll be right back.”</span>
</p><p>
  <span>“Okay,” Cas nods as Dean leaves. </span>
</p><p>
  <span>If Dean would have let him finish, Cas would have told him that he can actually clean them up using his grace. He never said anything before because he likes running off to the bathroom with Dean so they can wash each other. But now, Dean left him to wait on the bed and he doesn’t like that as much. </span>
</p><p>
  <span>“Here we go,” Dean slides back into the room and joins Cas on the bed. “It’s warm,” Dean says before touching Cas with the rag. </span>
</p><p>
  <span>“I wouldn’t notice either way,” Cas smiles at him. Dean looks a bit confused for a second then chuckles, delicately wiping up Cas’s come. “Did that feel good for you?”</span>
</p><p>
  <span>Dean rolls his eyes and looks at Cas, “Yes, duh.”</span>
</p><p>
  <span>“So then your orgasm was adequate?” Cas asks seriously. </span>
</p><p>
  <span>“Yes, Cas, my ‘orgasm was adequate.’” </span>
</p><p>
  <span>“Good,” Cas nods. “I thought you performed very well, thank you.”</span>
</p><p>
  <span>“Cas,” Dean smiles, shaking his head, “Dude,” Dean doesn’t know what to say. </span>
</p><p>
  <span>“You made me feel very good, </span>
  <em>
    <span>the best</span>
  </em>
  <span> I ever have… I just want to be sure that you also felt… Good.” </span>
</p><p>
  <span>“I felt,” Dean finishes wiping Cas up, </span>
  <em>
    <span>“So good.”</span>
  </em>
  
</p><p>
  <span>“Good,” Cas smiles and sits up. “I was unsure.”</span>
</p><p>
  <span>“You seriously couldn’t tell?” Dean asks, setting the rag on his side table. “I came </span>
  <em>
    <span>embarrassingly</span>
  </em>
  <span> fast.”</span>
</p><p>
  <span>“I don’t think it’s anything to be embarrassed about…” Cas tilts his head. </span>
</p><p>
  <span>“You’re right… I guess.” Dean smiles and leans into Cas to kiss him. </span>
</p><p>
  <span>After a few moments of them kissing, Cas wraps his arms around Dean and pulls him down on top of him, laying on the bed again and they stop kissing. “I’ve always felt… </span>
  <em>
    <span>Somewhat </span>
  </em>
  <span>connected to you, Dean,” Cas starts. “And of course, more recently that has intensified,” Dean blushes. “But… I feel… So close to you right now. And… I hope to always feel like this.”</span>
</p><p>
  <span>Dean smiles, “Cas,” Dean forces back a chuckle, “We </span>
  <em>
    <span>are</span>
  </em>
  <span> close,” Dean jokes. </span>
</p><p>
  <span>“No,” Cas chuckles which means it’s okay if Dean does, “Not physically close… I know we are </span>
  <em>
    <span>physically</span>
  </em>
  <span> close.” They are laying on top of each other after all. </span>
</p><p>
  <span>“I know what you mean Cas,” Dean smiles, “I was just messing around.”</span>
</p><p>
  <span>“You do?”</span>
</p><p>
  <span>“Yeah,” Dean nods and looks away, “‘Cause I feel it too…”</span>
</p><p>
  <span>“Dean,” Cas wraps his arms around him and rolls them over so he can be on top. “I’m glad we did this.”</span>
</p><p>
  <span>“Me too!” Dean smiles, “It was fun and we should do it again.”</span>
</p><p>
  <span>“Again, yes. Of course.” Cas nods sitting up. “Uhm,” Cas stands up and starts getting dressed again. “I guess I’ll leave you to sleep…”</span>
</p><p>
  <span>“Oh,” Dean nods, a bit disappointed. </span>
</p><p>
  <span>Cas puts his tie back on, “I’ll take the washcloth,” Cas says. </span>
</p><p>
  <span>“Thanks,” Dean starts getting under his blanket. Cas is about to leave anyway. </span>
</p><p>
  <span>“I will see you in the morning Dean,” Cas smiles, putting on his coat and picking up the rag, “And we can kiss more!”</span>
</p><p>
  <span>“Yeah,” Dean smiles. “I’ll… Kiss you in the morning.”</span>
</p><p>
  <span>“Not unless I kiss you before you get the chance.”</span>
</p><p>
  <span>“Is that a threat?” Dean smirks and asks in a playful way. </span>
</p><p>
  <span>“Maybe,” Cas smiles, turning off Dean's lamps. “Good night, Dean.”</span>
</p><p>
  <span>“Good night, Cas,” Dean sighs as he watches Cas leave. Pretty soon after, Dean falls asleep.</span>
</p><p> </p><p>
  <span>Then Dean is startled awake. “Cas?” Dean asks, confused, lowering his gun. </span>
</p><p>
  <span>“I didn’t mean to startle you, though I knew it would happen,” Cas grimaces. </span>
</p><p>
  <span>“Cas,” Dean smiles, finally adjusting, “I’m so sorry,” Dean sets his gun back away. “I didn’t mean to pull a gun on you…”</span>
</p><p>
  <span>“It’s alright,” Cas nods, sitting on the bed next to Dean. </span>
</p><p>
  <span>Dean sits up, “What time is it? Is everything okay?”</span>
</p><p>
  <span>“Everything is fine,” Cas nods. “But uhm… I was, thinking… And I know it’s a bit rude to wake you up to talk but…”</span>
</p><p>
  <span>“But you were thinking,” Dean chuckles, prompting Cas to continue. </span>
</p><p>
  <span>“Yes,” Cas smiles but then his face gets serious again. “Uhm,” Cas swallows. “Well, we decided if we wanted something we should just ask each other…”</span>
</p><p>
  <span>Cas kind of pauses. Dean doesn’t know where Cas is going with this, but if Cas woke him up to ask for a blowjob or something because he’s just </span>
  <em>
    <span>that horny…</span>
  </em>
  <span> Dean would actually find that extremely hot and would do it, hands down. </span>
</p><p>
  <span>“And,” Cas looks away for a second before making eye contact with Dean again. “Well, we are… Together. And we go on dates together, and we have sex together,” Dean smiles. He has no idea what Cas is talking about, but he likes it. “And I know that… When two people are together… They… Do certain things… Together…”</span>
</p><p>
  <span>“Okay,” Dean tilts his head in confusion.</span>
</p><p>
  <span>“Yes, well… I know you don’t like when I watch you sleep, so- And that is not what I am asking,” Cas shakes his head quickly. “I’m not asking to watch you sleep, I’m…” Cas breathes. “Nevermind,” Cas starts to get up. “Sorry I woke you up, go back to sleep-”</span>
</p><p>
  <span>“Wait,” Dean smiles, grabbing Cas’s arm. “Finish your speech-question-thing…”</span>
</p><p>
  <span>“That’s alright, it’s silly…”</span>
</p><p>
  <span>“Okay,” Dean smiles, “Uhm, Cas? Are you asking permission to sleep with me?”</span>
</p><p>
  <span>“Yes, but… I don’t sleep so… I don’t want to make you uncomfortable by laying awake next to you while you sleep…”</span>
</p><p>
  <span>“Well,” Dean forces back a laugh, “I don’t care about all that and I actually would </span>
  <em>
    <span>love</span>
  </em>
  <span> if you laid with me all night, so,” Dean smirks as Cas sits back down, “If you’re asking my permission… My answer is yes.”</span>
</p><p>
  <span>“You truly would enjoy it if I laid with you?”</span>
</p><p>
  <span>“Cas,” Dean rolls his eyes but it might be too dark to see that. “I </span>
  <em>
    <span>hate</span>
  </em>
  <span> sleeping alone. I want you in my bed every night from here on out, I just hope you don’t get bored.”</span>
</p><p>
  <span>“I won’t get bored,” Cas notes. </span>
</p><p>
  <span>“Okay,” Dean smiles. “I’m glad you woke me up then.” </span>
</p><p>
  <span>“So I can stay?” Cas clarifies. </span>
</p><p>
  <span>“No,” Dean chuckles, “Now you </span>
  <em>
    <span>have</span>
  </em>
  <span> to stay.” Cas smiles. “Take off most of your clothes,” Dean suggests. “Then we can…” Dean rolls his eyes. “Snuggle or whatever.”</span>
</p><p>
  <span>Cas starts taking his clothes off. “And that requires the removal of my clothes?” Cas asks.</span>
</p><p>
  <span>“Yes,” Dean nods. </span>
</p><p>
  <span>“I feel like that is untrue.”</span>
</p><p>
  <span>“Well,” Dean chuckles. “I want you to be pretty much as naked as possible if you’re gonna press up into me.”</span>
</p><p>
  <span>“That sounds fair.” Cas is finally in his briefs. </span>
</p><p>
  <span>“Good,” Dean lifts up his blanket for Cas to get under with him. “Wanna spoon?” Dean asks, then blushes. </span>
</p><p>
  <em>
    <span>“Do I want a spoon?</span>
  </em>
  <span> Why do I need a spoon?”</span>
</p><p>
  <span>“No, that’s not-”</span>
</p><p>
  <span>“Do </span>
  <em>
    <span>you</span>
  </em>
  <span> want one? I can get you one if you want one…”</span>
</p><p>
  <span>“No, Cas,” Dean chuckles. “It’s like uh,” He’s trying to think of a good way to explain this. “It’s pretty much </span>
  <em>
    <span>the best</span>
  </em>
  <span> position to like… Cuddle or whatever.”</span>
</p><p>
  <span>“How does it work?” Cas asks. </span>
</p><p>
  <span>“Well, you know how spoons kinda fit together?” Dean puts his hands on top of each other to demonstrate. “Like- Like the cuppy parts fit together… You know?” Cas doesn’t reply so Dean tries to keep explaining. “Okay,” Dean huffs, “So basically, let’s say </span>
  <em>
    <span>you</span>
  </em>
  <span> are gonna spoon </span>
  <em>
    <span>me,</span>
  </em>
  <span> uhm,” Dean swallows. “We’d both be laying down and like, on our sides and </span>
  <em>
    <span>you’re</span>
  </em>
  <span> pressed up against me- Like your front against my back- And you can just like, put your arms around me and,” Dean shrugs. “Well that’s kind of it. It’s not too complicated.”</span>
</p><p>
  <span>“Do we kiss?” Cas asks.</span>
</p><p>
  <span>“Not… </span>
  <em>
    <span>Particularly.”</span>
  </em>
  <span> Dean shakes his head. “No.”</span>
</p><p>
  <span>“And I am supposed to hold you? Where? Your waist?”</span>
</p><p>
  <span>“Anywhere,” Dean swallows. “Anywhere you want. And if you want, you know, your hands can wander. Or, sometimes it’s nice to… Hold hands.”</span>
</p><p>
  <span>“Are our bodies </span>
  <em>
    <span>completely</span>
  </em>
  <span> pressed together?” Cas asks. </span>
</p><p>
  <span>“Yeah,” Dean mumbles. </span>
</p><p>
  <span>“And you </span>
  <em>
    <span>like</span>
  </em>
  <span> this?”</span>
</p><p>
  <span>“Yes!” Dean says quickly. “Well, uhm- I’d say prob- Probably the uh, the normal amount,” Dean shrugs, “You know. Not more than normal, if that’s what you’re asking. It’s nice. I get the appeal. It’s fine. The normal amount.”</span>
</p><p>
  <span>“Dean,” Cas chuckles. “Do you like this?” He asks again. </span>
</p><p>
  <span>“I </span>
  <em>
    <span>love</span>
  </em>
  <span> it,” Dean blushes. </span>
</p><p>
  <span>“And can you sleep like this? Or is it just for cuddling while we are awake?”</span>
</p><p>
  <span>“Sleep,” Dean clears his throat, “Can definitely sleep like this.”</span>
</p><p>
  <span>“Hm,” Cas nods. “It sounds intimate.”</span>
</p><p>
  <span>Dean freezes and gets nervous because of how quiet it is. “Well, ugh,” Dean nervous laughs, “We don’t </span>
  <em>
    <span>have </span>
  </em>
  <span>to. It was just, you know,” He laughs again, “Just an idea.” He shrugs as casually as possible. </span>
</p><p>
  <span>“Okay.” Neither of them move. “Wait,” Cas starts, “Does that mean you do not wish to do it?”</span>
</p><p>
  <span>“Well-”</span>
</p><p>
  <span>“Because I am interested in trying.”</span>
</p><p>
  <span>“Oh,” Dean smiles, “Well, come ‘ere…” </span>
</p><p>
  <span>Cas bites his lips and scoots closer to Dean then wraps his arms around him. Dean is a </span>
  <em>
    <span>bit</span>
  </em>
  <span> surprised that Cas wrapped around </span>
  <em>
    <span>him,</span>
  </em>
  <span> but that </span>
  <em>
    <span>is</span>
  </em>
  <span> how he described it, so of course this is what Cas did. “Okay,” Dean chuckles, scooching his butt back against Cas a bit. “So, uhm, you’re called the big spoon, the person on the outside…”</span>
</p><p>
  <span>“And you are what? The small spoon?” Cas asks.</span>
</p><p>
  <span>Dean chuckles, “Little spoon,” He corrects then immediately blushes.</span>
</p><p>
  <span>“Which do you prefer to be?” Cas asks. “Because I quite enjoy holding you.”</span>
</p><p>
  <span>“I don’t have a preference,” Dean closes his eyes.</span>
</p><p>
  <span>“Truly?” Cas asks. </span>
</p><p>
  <span>“I honestly don’t know,” Dean chuckles. “Both are… Nice.”</span>
</p><p>
  <span>“This is very soothing, I can see why you think it’s the best.”</span>
</p><p>
  <span>Dean feels oddly comfortable like this. Like a warm, protective hug that lasts all night. He finds Cas’s hand to hold onto then mumbles, “Good night,” one last time before he slowly drifts off, glad that Cas is finally in bed with him. </span>
</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Okay, so I have these ideas for short little fluff pieces with these two. Like really short, and JUST fluff. Would y'all be interested in reading those? </p><p>Comment if you want! I love hearing what y'all say! I'm a little behind with replying to all of them right now, but I see them! And I will reply! I've just been a bit busy!</p></blockquote></div></div>
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